Chicago Twenty Something | Chicago's Best Events
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ALL EVENTS

JANUARY

- Chicago Rosé Fest
- Mac & Cheese Crawl

- Hard Seltzer Fest
​​- Adults Night at the Trampoline Park
- Cocktail Cruises
​
- Chicago Bar Crawl Experiences

- Check Back As New Events Are Always Being Added

FEBRUARY

- Chicago Whiskey Festival
- Country Day Party
- The Pajama Crawl

​- Adults Night at the Trampoline Park
​
​- Chicago Bar Crawl Experiences
​- Check Back As New Events Are Always Being Added

MARCH

- Chicago Shamrock Crawl
- Green River Crawl

- 
Country Day Party
​
- Chicago Wine Fest
​- Adults Night at the Trampoline Park
​- Cocktail Cruises
​- Chicago Bar Crawl Experiences
- Check Back As New Events Are Always Being Added

APRIL

- Chicago Donut Fest
- Chicago Beer Fest
​- Chicago Whiskey Festival

- Boy Band Bar Crawl
​- Adults Night at the Trampoline Park
- Cocktail​ Cruises
​- Chicago Bar Crawl Experiences
- Check Back As New Events Are Always Being Added

MAY

- Bar Crawl De Mayo
- Day Party De Mayo
- Chicago Brunch Crawl

​- Adults Night at the Trampoline Park
- Sangria Fest on The Beach
- Cocktail Cruises
​- Chicago Bar Crawl Experiences
- Check Back As New Events Are Always Being Added

JUNE

- Chicago Rosé Day
- Sox Crawl
- Sangria Fest on the Beach
- Wine Fest on the Beach
- Whiskey Festival on the Beach
- Beer Fest on The Beach
- Sangria Fest on The Beach

​- Adults Night at the Trampoline Park
- Cocktail Cruises
​- Chicago Bar Crawl Experiences
- Check Back As New Events Are Always Being Added

JULY

- The Mustache Crawl
- Night at the Zoo

- Adults Night at the Trampoline Park
- Cocktail Cruises
​- Chicago Bar Crawl Experiences
- Check Back As New Events Are Always Being Added

AUGUST

- The Taco Crawl
​
- Chicago Mimosa Crawl 

- Adults Night at the Trampoline Park
-
Cocktail Cruises
​- Chicago Bar Crawl Experiences
- Check Back As New Events Are Always Being Added

SEPTEMBER

- Sox Crawl
- Dessert Fest at the Zoo
- Chicago Country Crawl

- Rosé Fest on The Beach
- Wine Fest on The Beach
- Whiskey Festival on The Beach
​- Oktoberfest on The Beach
​
- Adults Night at the Trampoline Park

- Cocktail Cruises
​- Chicago Bar Crawl Experiences
​- Check Back As New Events Are Always Being Added

OCTOBER

- Chicago Rosé Fest
- Halloween Day Crawl
- River North Halloween Crawl
- Wrigleyville Halloween Crawl
​- Adults Night at the Trampoline Park
​
- Halloween Cruises

- All Halloween Events
​- Chicago Bar Crawl Experiences
- Check Back As New Events Are Always Being Added

NOVEMBER

- Whiskey Festival at the Godfrey
- Adults Night at the Trampoline Park
- Chicago Pizza Crawl

- The Turkey Crawl
​- Chicago Bar Crawl Experiences
- Check Back As New Events Are Always Being Added

DECEMBER

- Holiday Cocktail Festival
- TBOX: Chicago's Christmas Crawl
​
- Santa Cruises
- Chicago Wine Fest

- Matzo Bash
- NOVA New Year's Eve
​
- Zoo Year's Eve

- All New Year's Events
​
- New Year's Eve Cruises
​- Chicago Bar Crawl Experiences
- Check Back As New Events Are Always Being Added

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